Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 2-Amino-4,6-dimethoxypyrimidine, blongs to pyrimidines compound. Safety of 2-Amino-4,6-dimethoxypyrimidine

One pot procedure for the synthesis of 2-amino-5,7-dimethoxy [1,2, 4] triazolopyrimidine (ADTP) from 2-amino-4,6-dimethoxypyrimidine (ADP) 11. 9 g (0.075 mol) ADP was dissolved in 68 g ethyl acetate. 11 g (0.0825 mol) ethoxycarbonyl isothiocyanate was added within 20 min. at 78C (no exotherm). The mixture was stirred over 5 h at reflux (78-79C). 49.2 g (0.075 mol) hydroxylammonium sulfate (25 % solution in water) were added and the mixture heated to 71C (reflux aceotrope). 50 g (0.1 mol) diluted caustic soda (2 mot/1) was added within 1 h to establish the pH from 1.3 to 6.5 and hold at 6.5-7. 0 (offgas C02 and H2S, slightly exotherm). The mixture was stirred over 6 h under reflux (71C) for reaction completion. The mixture was cooled down over night to 20C. The product (ADTP) was filtrated and washed 3 times with each 25 g water to remove the salt (Na content after first wash 0.42 %, after second 0.20 %, after third 0.025 %). Finally the solid ADTP was dried. Yield : 91.1 % in respect to ADP, purity 95.3 % (quantitative HPLC assay).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2005/63753; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 633328-98-0, name is 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine, molecular formula is C5H3ClN4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. name: 5-Chloro-1H-pyrazolo[4,3-d]pyrimidine

NaH in mineral oil (570 mg, 14 mmol) was slowly added at 0 C. to a solution of 5-chloro-1H-pyrazolo[4,3-d]pyrimidine (2.0 g, 13 mmol) and [beta-(trimethylsilyl)ethoxy]methyl chloride (2.40 mL, 13.6 mmol) in tetrahydrofuran (25 mL). After stirring at r.t. for 1 h, the reaction mixture was quenched by the addition of water and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. The solvents were evaporated under reduced pressure and the crude product was purified by Biotage Isolera (2.36 g, 64%). LCMS calculated for C11H18ClN4OSi (M+H)+ m/z=285.1; found 285.2

With the rapid development of chemical substances, we look forward to future research findings about 633328-98-0.

Reference:
Patent; Incyte Corporation; Vechorkin, Oleg; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; Hummel, Joshua; (117 pag.)US2018/72741; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5604-46-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 112a (253 mg, 1.1 mmol) and 112b (192 mg, 1.0 mmol) was added DMF (20 ml) and the reactionmixture was stirred at room temperature overnight. Thenpoured the mixture into ice/saturated sodium bicarbonatesolution (40 ml). The precipitated solid was collected by filtration and washed with watet The solid was taken in DMF (10 ml) and added gl. acetic acid (10 drops). Thereaction mixture was stirred at room temperature overnightand processed as above. The solid thus obtained (223 mg)was taken in dichloromethane (10 ml) and treated with DDQ (138 mg, 0.6 mmol) at room temperature for 1 hr. The reaction mixture was diluted with chloroform (30 ml) and washed with saturated sodium bicarbonate solution (50 ml). Separated the organic layer, and the aqueous layer was extracted with EtOAc (50 ml). Combined the organic layers, dried (Na2 SO4), filtered and concentrated to provide 11 2cwhich was taken further without any purification. Conversion of 112c (0.6 mmol) to required product 112 followed procedures described above (Procedure H, Step 3). Crude 112 thus obtained was treated with excess di-tert-butyl dicarbonate (440 mg), catalytic DMAP (10 mg) in THF (8ml) at room temperature, overnight. The reaction mixture was processed using EtOAc (50 ml) and brine (50 ml). The organic layer was separated, dried (Na2504), filtered and concentrated. The residue was purified using silica gel (prepacked, 40 g cartridge) with 20/80 to 70/30 of EtOAc/ hexanes. This resulted in 32 mg of product containing two t-boc groups. This material was deprotected with 4M HC1 in dioxane (5 ml) at room temperature, overnight. The reaction mixture was concentrated, and the residue purified using silica gel (prepacked, 12 g cartridge) with 1/99 to 12/88 of MeOH/chloroform to provide 6 mg of 112 as a light brown solid.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5604-46-6, 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; Merck Sharp & Dohme Corp.; Southern Research Institute; Arasappan, Ashok; Njoroge, F. George; Kwong, Cecil D.; Ananthan, Subramaniam; Bennett, Frank; Velazquez, Francisco; Girijavallabhan, Vinay M.; Huang, Yuhua; Kezar, III, Hollis S.; Maddry, Joseph A.; Reynolds, Robert C.; Roychowdhury, Abhijit; Fowler, Anita T.; Secrist, III, John A.; Kozlowski, Joseph A.; Shankar, Bandarpalle B.; Tong, Ling; Kim, Seong Heon; MacCoss, Malcolm; Venkatraman, Srikanth; Verma, Vishal; (798 pag.)US9433621; (2016); B2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 153286-94-3, name is 5-Ethynylpyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 153286-94-3

To a mixture of (5)-3-(l-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-8-ehloro- 2-phenylisoquinoim-l(2//)-one (50.8 mg, 0.0981 mmol), Cul (2.2 mg, 0.012 mmol), and Pd(PPh3)2Cl2 (14.3 mg, 0.020 mmol) in anhydrous DMF (2 ml) was added 5-ethynylpyrimidine (31.6 mg, 0.304 mmol), and followed by the addition of tri ethyl amine (0.05 mL, 0.40 mmol). The resulted solution was heated to 75 C and stirred further for 5 hours, then cooled to rt, and quenched with water (15 mL), The resulted mixture was extracted with DCM (30 mL x 3), and the combined organic phases were washed with saturated brine (20 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) :::: 100/5) to give the title compound as a yellowish solid (30 mg, yield 41.3%). MS (ESI, pos. ion) m/z: 494.2 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (600 MHz, OMSO-de) delta (ppm): 9.12 (d, J = 6.4 Hz, 2H), 7.89 (s, 1H), 7.60 (d, J = 3.9 Hz, 2H), 7.55-7.32 (m, 7H), 6.88 (d, J = 6.7 Hz, 2H), 6.75 (s, 1H), 4.75-4.61 (m, 1H), 1.33 (d, 3H).

The synthetic route of 153286-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 7752-82-1 ,Some common heterocyclic compound, 7752-82-1, molecular formula is C4H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a solution of 5-bromopyrimidin-2-amine (11 mmol, 2.0 g) in acetic acid (35 mL) was added sodium nitrite (69 mmol, 4.8 g) in water (25 mL) at RT over 1.5 h. After 5 h, the reaction mixture was partially evaporated, the precipitate was filtered and washed with water to give the title compound. MS (ESI) m/z = 175, 177 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7752-82-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SAKURADA, Isao; HIRABAYASHI, Tomokazu; MAEDA, Yoshitaka; NAGASUE, Hiroshi; MIZUNO, Takashi; XU, Jiayi; ZHANG, Ting; SMITH, Cameron; PARKER, Dann; WO2015/160634; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 4983-28-2, Adding some certain compound to certain chemical reactions, such as: 4983-28-2, name is 2-Chloro-5-hydroxypyrimidine,molecular formula is C4H3ClN2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4983-28-2.

Intermediate 25: 2-Chloro-5-(3-methoxyphenoxy)pyrimidine A mixture of 2-chloro-5-hydroxypyrimidine (l .Og, 7.66mmol), 3-methoxyphenyl boronic acid (1.16g, 7.66mmol), copper (II) acetate (1.39g, 7.66mmol), triethylamine(5.34mL, 7.66mmol) and powdered 4A molecular sieves in dichloromethane (30mL) was stirred under air for 3 days. A calcium chloride guard tube was used to protect the reaction from moisture. The reaction mixture was diluted with dichloromethane, filtered and washed with water and brine. The organic phase was dried (MgS04), the solvent removed under reduced pressure and the crude product was purified by flash chromatography, using 0-15percent ethyl acetate:hexane as eluent, to provide 2-chloro-5- (3-methoxyphenoxy)-pyrimidine (0.448g, 25percent) as yellow oil.Mass: (ES+) 237 (M+H)+ NMR: deltaEta (CDC13) 3.82 (3H, s), 6.63 (2H, m), 6.81 (IH, br d), 7.33 (IH, t) and 8.39 (2H, s).

According to the analysis of related databases, 4983-28-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David Christopher; SCOPES, David Ian Carter; WO2011/144578; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 1627-28-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1627-28-7, name is 6-Chloro-5-methylpyrimidine-2,4(1H,3H)-dione. This compound has unique chemical properties. The synthetic route is as follows.

A stirred solution of 6-chloro-5-methylpyrimidine-2,4(1 H,3H)-dione a5 (4.80 g, 0.30 mmol) and Nal (23.4 g, 150 mmol) in HI (60 mL) was stirred in sealed tube at room temperature for 66 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was filtered and washed with cold water (50 mL) and dried under vacuum to afford 2.1 g of 6-iodo-5-methylpyrimidine-2,4(1 H,3H)-dione a6 was isolated as a brown solid, which was used in next step without any further purification. LCMS (ES+): 253 (M+H)+. 1H NMR (400 MHz, DMSO -cfe) 5 1 1.21 (s, 1 H), 1 .90 (s, 3H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1627-28-7, 6-Chloro-5-methylpyrimidine-2,4(1H,3H)-dione.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; VALADE, Anne; VERMEIREN, Celine; WOOD, Martyn; MAGUIRE, Ralph; (52 pag.)WO2019/105913; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 131860-97-4, blongs to pyrimidines compound. Product Details of 131860-97-4

EXAMPLE 4 A solution of the potassium salt of 2-cyanophenol was prepared by mixing 2-cyanophenol (13.2 g) and potassium hydroxide (6.8 g) in water (7 g). This solution was added to (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (32.8 g) over 5 minutes while maintaining the temperature at 95-100 C. The resulting mixture was stirred at 120-20 C. for 2 hours. The reaction mixture was mixed with water and toluene and the organic layer separated. The toluene solution contained (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (61.5% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, and friends who are interested can also refer to it.

Reference:
Patent; ZENECA Limited; US6153750; (2000); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 57054-92-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 57054-92-9, name is 5-Bromo-2-chloro-4-methoxypyrimidine, molecular formula is C5H4BrClN2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of 5-bromo-2-chloro-4-methoxypyrimidine (Intermediate 60, 60 mmol, 13.5 g) and 3-chloro-4-fluoroaniline (60.3 mmol, 9.23 g) in acetonitrile (140 mL), 4 M HCl in 1,4-dioxane (14 mL) was added dropwise. The resulting solution was refluxed at 100 C with constant stirring. The solvent was removed in vacuo and the residue was basified with 10% NaHCO3 solution, then extracted with ethyl acetate (2 x 250 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (silicagel, 60-120 mesh) using 5% EtOAc in hexane to yield (5-bromo-4-methoxy-pyrimidin-2-yl)-(3-chloro-4-fluoro- phenyl)-amine as a white solid in 70 % yield (42 mmol, 14 g). MS(ES): 332 (M) for CnH8BrClFN3O.1H-NMR (400 MHz, DMSO-d6): delta 4.0 (s, 3H), 7.37 (t, J= 9.20 Hz, IH), 7.62 (ddd, J = 9.02, 4.12, 2.84 Hz, IH), 8.04 (dd, J= 6.80, 2.60 Hz, IH), 8.41 (s, IH), 9.94 (s, IH).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 57054-92-9, 5-Bromo-2-chloro-4-methoxypyrimidine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BORIACK-SJODIN, Ann; CARCANAGUE, Daniel, Robert; DUSSAULT, Daemian, David; HATOUM-MOKDAD, Holia; HULL, Kenneth, Gregory; IOANNIDIS, Georgine; MANCHESTER, John, Irvin; McGUIRE, Helen, Maureen; McKINNEY, David, Charles; STOKES, Suzanne; WO2010/38081; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 33097-13-1 ,Some common heterocyclic compound, 33097-13-1, molecular formula is C6H3Cl2N3S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

[0440] Step 1 : To a suspension of 4,6-dichloro-2-(methylthio)pyrimidine-5-carbonitrile (330 mg, 1.5 mmol) in DMF (3 mL) was added 4-iodoaniline (361 mg, 1.65 mmol). After stirring at room temperature for 3 h, the mixture was diluted with water, the resulting precipitate was collected by filtration to give 4-chloro-6-(4-iodophenylamino)-2- (methylthio)pyrimidin-5-carbonitrile (541 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33097-13-1, its application will become more common.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; XU, Qing; HUANG, Wolin; JIA, Zhaozhong J.; SONG, Yonghong; WO2012/61415; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia